Antibiotic CC-1065 is disclosed and claimed in L. J. Hanka et al U.S. Pat. No. 4,169,888 together with a process for preparing antibiotic CC-1065 by aerobic fermentation procedures, and recovering antibiotic CC-1065 therefrom.
In J. Am. Chem. Soc., 103, No. 18, 1981, W. Wierenga published a "Synthesis of the Left-Hand Segment of the Antitumor Agent CC-1065".
Wierenga U.S. Pat. No. 4,400,518 claims some new compounds of the formula ##STR2## wherein R.sub.2 and R.sub.3 are hydrogen, C.sub.1 to C.sub.5 alkyl, or phenyl;
R.sub.4 is --SO.sub.2 R.sub.2, --SO.sub.2 CH.sub.2 C(O)phenyl, --CO.sub.2 CH.sub.2 Z where PA0 Z is --CH.sub.2 I, --CCl.sub.3, --CH.sub.2 SO.sub.2 R.sub.2, phenyl or fluorenyl; PA0 X is --OSO.sub.2 R.sub.2, Cl, Br or I, PA0 R.sub.2 and R.sub.3 are hydrogen, C.sub.1 to C.sub.5 -alkyl, or phenyl; PA0 R.sub.4 is --SO.sub.2 R.sub.2, --SO.sub.2 CH.sub.2 C(O)phenyl, --CO.sub.2 CH.sub.2 Z where PA0 Z is iodomethyl, trichloromethyl, --CH.sub.2 SO.sub.2 R.sub.2, phenyl or fluoroenyl; and PA0 X is --OSO.sub.2 R.sub.2, chloro, bromo or iodo, with the proviso that R.sub.2 cannot be hydrogen when it is adjacent to --SO.sub.2. PA0 R.sub.4 is --SO.sub.2 R.sub.2, --SO.sub.2 CH.sub.2 C(O)phenyl or --CO.sub.2 CH.sub.2 Z where PA0 Z is iodomethyl, trichloromethyl, --CH.sub.2 SO.sub.2 R.sub.2, phenyl or fluorenyl; by cyclizing its halomethyl or its methanesulfonate ester precursor compound. PA0 R.sub.4 is --SO.sub.2 R.sub.2, --SO.sub.2 CH.sub.2 C(O)phenyl, or --CO.sub.2 CH.sub.2 Z where PA0 Z is iodomethyl, trichloromethyl, --CH.sub.2 SO.sub.2 R.sub.2, phenyl or fluorenyl, and PA0 Z is --OSO.sub.2 R.sub.2, chloro, bromo or iodo, with the proviso that R.sub.2 cannot be hydrogen when it is adjacent to --SO.sub.2. PA0 R.sub.2 and R.sub.3 are hydrogen, C.sub.1 to C.sub.5 -alkyl or phenyl; PA0 R.sub.4 is --SO.sub.2 R.sub.2, --SO.sub.2 CH.sub.2 C(O)phenyl, or --CO.sub.2 CH.sub.2 Z where PA0 Z is iodomethyl, trichloromethyl, --CH.sub.2 SO.sub.2 R.sub.2, phenyl or fluorenyl. PA0 R.sub.1 in formula II is CH.sub.3 --, --CH.sub.2 Ph, CH.dbd.CHCH.sub.2 --, --CH.sub.2 SCH.sub.3, --CH.sub.2 OCH.sub.3, --CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3, --CH.sub.2 CCl.sub.3, --CH.sub.2 CH.sub.2 Si(R.sub.2).sub.3, or H, where Ph is phenyl; PA0 R.sub.2 is alkyl(C.sub.1 -C.sub.5), phenyl, or H; PA0 R.sub.2 ' is C.sub.1 to C.sub.5 -alkyl, phenyl or hydrogen, and is not necessarily the same as R.sub.2 in one compound; PA0 R.sub.3 is alkyl(C.sub.1 -C.sub.5), phenyl, or H; PA0 X is Cl, Br, or I--, or OSO.sub.2 R.sub.40, where R.sub.40 is C1 to C.sub.5 -alkyl, phenyl, tolyl, bromophenyl, nitrophenyl, or trifluoromethyl; PA0 R.sub.50 is hydrogen or the same as R.sub.5 ; PA0 R.sub.5 is a carbonyl acyl group selected from the group consisting of PA0 1,2,8,8a-tetrahydro-7-methyl-2-(quinolinylcarbonyl)cyclopropa[c]pyrrolo[3,2 -e]indol-4(5H)-one (U-68,749); PA0 1,2,8,8a-tetrahydro-7-methyl-2-(2-pyrrolylcarbonyl)cyclopropa[c]pyrrolo[3,2 -e]indol-4(5H)-one (U-68,819); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[[5-benzoylamino-1H-indol-2-yl]carbonyl]cycl opropa[c]pyrrolo[3,2-e]indol-4(5H)-one (U-68,846); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[[5-[[5-benzoylamino-1H-indol-2-yl)carbonyl] amino]-1H-indol-2-yl]carbonyl]cyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one (U-68,880); PA0 1,2,8,8a-tetrahydro-7-methyl-2-(1H-indol-2-ylcarbonyl)cyclopropa[c]pyrrolo( 3,2-c]indol-4(5H)-one (U-66,694); PA0 1,2,8,8a-tetrahydro-7-methyl-2-benzoylcyclopropa[c]pyrrolo[3,2-e]indol-4(5H )-one (U-66,866); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[(6-hydroxy-7-methoxy-1H-indol-2-yl)carbonyl ]cyclopropa[c]pyrrolo[3,2-e]indol-4(5H)-one (U-67,785); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[[5-[[[1H-indol-2-yl]carbonyl]amino]-1H-indo l-2-yl]carbonyl]cyclopropa[c]pyrrolo]3,2-e]indol-4(5H)-one (U-68,415); PA0 (1,2,8,8a)-tetrahydro-7-methyl-2-2[[5-cyanoamino-1H-indol-2-yl]carbonyl]cyc lopropa[c]pyrrolo[3,2-e]indol-4(5H)-one (U-69,058); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[[5-ureido-1H-indol-2-yl]carbonyl]cyclopropa [c]pyrrolo[3,2-e]indol-4(5H)-one (U-69,059); PA0 1,2,8,8a-tetrahydro-7-methyl-2-[[5-[[[5-ureido-1H-indol-2-yl]carbonyl]amino ]-1H-indol-2-yl]carbonyl]cyclopropa[c]pyrrolo[3,2-a]indol-4(5H)-one (U-69,060).
with the proviso that R.sub.2 cannot be hydrogen when it is adjacent to --SO.sub.2.
Wierenga U.S. Pat. No. 4,413,132 claims some compounds of the formula ##STR3## where R.sub.1 is methyl, benzyl, allyl, methylthiomethyl, methoxymethyl, methoxyethoxymethyl, 2,2,2-trichloroethyl, or (R.sub.2).sub.3 -Si-ethyl,
Wierenga U.S. Pat. No. 4,423,228 claims a process for preparing an intermediate compound of the formula ##STR4## by reacting its 1-methanol pecursor with triphenylphosphine/carbon tetrahalide, and then recovering the above cyclopropa- compound from its reaction mixture.
Wierenga U.S. Pat. No. 4,423,229 claims a process for preparing a compound of the formula ##STR5## where R.sub.2 and R.sub.3 are hydrogen, C.sub.1 to C.sub.5 -alkyl or phenyl;
Wierenga U.S. Pat. No. 4,423,230 claims a process for preparing a compound of the formula ##STR6## where R.sub.2 and R.sub.3 are hydrogen, C.sub.1 to C.sub.5 -alkyl, or phenyl;
Wierenga U.S. Pat. No. 4,424,365 claims compounds of the formula ##STR7## in the keto or enol form, where